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WO2018096008A1 - Composition comprenant des composés d'avermectine sans corps gras solides - Google Patents

Composition comprenant des composés d'avermectine sans corps gras solides Download PDF

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Publication number
WO2018096008A1
WO2018096008A1 PCT/EP2017/080146 EP2017080146W WO2018096008A1 WO 2018096008 A1 WO2018096008 A1 WO 2018096008A1 EP 2017080146 W EP2017080146 W EP 2017080146W WO 2018096008 A1 WO2018096008 A1 WO 2018096008A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
dermatological
pharmaceutical composition
weight
avermectin compounds
Prior art date
Application number
PCT/EP2017/080146
Other languages
English (en)
Inventor
Claire Mallard
Original Assignee
Nestlé Skin Health Sa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nestlé Skin Health Sa filed Critical Nestlé Skin Health Sa
Priority to US16/463,810 priority Critical patent/US10744147B2/en
Priority to EP17803935.0A priority patent/EP3544587A1/fr
Publication of WO2018096008A1 publication Critical patent/WO2018096008A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles

Definitions

  • composition comprising avermectin compounds without solid fatty substances
  • the invention relates to a dermatological or pharmaceutical composition
  • a dermatological or pharmaceutical composition comprising at least one active compound chosen from avermectin compounds with less than 3 % by weight o f solid fatty substances at room temperature and at atmospheric pressure.
  • the invention relates to a dermatological or pharmaceutical composition
  • a dermatological or pharmaceutical composition comprising at least one aqueous phase and at least one active phase comprising at least one active compound chosen from avermectin compounds and at least one so lvent and/or propenetrating agent of avermectin compounds, where the composition comprises less than 3 % by weight of solid fatty substances at room temperature and at atmospheric pressure, relative to the total weight of the composition.
  • the invention relates also to the composition for use in the treatment of rosacea, o f common acne, of seborrheic dermatitis, o f perioral dermatitis, o f acneiform rashes, of transient acantholytic dermatosis, o f acne necrotica miliaris and o f atopic dermatitis, and preferably for use in the treatment of rosacea.
  • the invention relates to a method for preparing the composition.
  • avermectins a group of macrocyclic lactones produced by the bacterium Streptomyces avermitilis (Reyno lds JEF (Ed) ( 1993) Martindale, The extra pharmacopoeia, 29 th Edition, Pharmaceutical Press, London), namely includes ivermectin, invermectin, avermectin, abamectin, doramectin, eprinomectin, and selamectin.
  • ivermectin is a mixture o f two compounds, 5 -0- demethyl-22,23 -dihydroavermectin A l a and 5 -0-demethyl-22-23 - dihydroavermectin An,.
  • ivermectin was presented as a broad-spectrum anti-parasitic medicinal product for veterinary use (W. C . CAMPBELL, et al. , ( 1983 ) "Ivermectin: a potent new anti-parasitic agent", Science, 221 , 823 -828) .
  • Ivermectin is more particularly an anthelmintic. It has been administered in humans in the treatment of onchocerciasis caused by onchocerca vo lvulus, o f gastrointestinal strongyloidias (anguillulosis) and o f human scabies and also in the treatment of micro filaremia diagnosed or suspected in individuals suffering from lymphatic filariosis due to Wuchereria bancrofti .
  • compounds o f avermectin family have been used in the treatment o f dermatological conditions such as rosacea in a topical pharmaceutical composition suited for human administration.
  • topical compositions comprising ivermectin for the treatment o f dermatological conditions such as rosacea which are in addition chemically and physically stable over time.
  • compositions are in the form of a cream with a high viscosity usually ranging from 40 Pa.s to 90 Pa. s, and therefore are not pourable which limits their ability to be sprayable using either a mechanic pump spray or a pressurized spray.
  • compositions comprising avermectin compounds, especially ivermectin, which are pourable and sprayable without impeding on their chemical and physical stability over time.
  • a liquid is pourable if it flows and conforms to its container at room temperature . It displays Newtonian or pseudoplastic flow behavior.
  • a semisolid is not pourable if it does not flow or conform to its container at room temperature . It does not flow at low shear stress and generally exhibits plastic flow behavior.
  • a dermatological or pharmaceutical composition comprising at least one active compound chosen from avermectin compounds where the composition comprises less than 3 % by weight of so lid fatty substances at room temperature and at atmospheric pressure, relative to the total weight o f the composition, is pourable while having good chemical and physical stability over time.
  • the present invention thus concerns a dermatological or pharmaceutical composition
  • a dermatological or pharmaceutical composition comprising at least one aqueous phase and at least one active phase comprising at least one active compound chosen from avermectin compounds and at least one so lvent and/or propenetrating agent of avermectin compounds, where the composition comprises less than 3 % by weight of solid fatty substances at room temperature and at atmospheric pressure, relative to the total weight o f the composition.
  • the composition according to the invention has a viscosity ranging from 1000 to 10000 cP, in particular ranging from 1000 to 5000 cP measured at room temperature using a Brookfield LV and therefore is pourable.
  • the composition according to the invention has a yield stress ranging from 5 Pa to 50 Pa, preferably from 1 0 to 20 Pa at room temperature using a Malvern rheometer.
  • the composition according to the invention is sprayable using either a mechanic pump spray or a pressurized spray making its application easier on the skin.
  • the texture of the composition is light.
  • composition according to the invention exhibits good chemical and physical stability over time, even at a temperature above ambient temperature (for example, 40°C) .
  • “Chemical stability” means that the amount o f avermectin compounds o f the composition does not change more than 5 % by weight relative to the initial amount in avermectin compounds o f the composition.
  • “Physical stability” means that the composition meets the acceptance criteria for appearance, physical attributes and functionality test (e. g. co lor, phase separation, dose delivery per actuation) . More precisely, the physical stability means that at least two of the fo llowing criteria, preferably all o f the fo llowing criteria : microscopic aspect, macroscopic aspect, viscosity and pH, do not significantly vary after manufacture time during 1 month, preferably during 2 months and even more preferably during 3 months .
  • composition of the present invention is in the form o f a pourable fluid emulsion wherein the active compound is fully so lubilized in the composition while remaining chemically and physically stable over time, especially without formation of crystals.
  • the present invention also concerns the dermatological or pharmaceutical composition as defined above for use in the treatment of rosacea, o f common acne, o f seborrheic dermatitis, o f perioral dermatitis, of acneiform rashes, o f transient acantholytic dermatosis, of acne necrotica miliaris and o f atopic dermatitis, and preferably for use in the treatment of rosacea.
  • the invention concerns also a method for preparing the composition comprising the following steps :
  • active phase refers to the phase comprising the active compound.
  • the composition o f the present invention it has been observed that the avermectin compounds have been so lubilized in the active phase despite o f the fact that the said active phase comprises a low amount of so lid fatty substances .
  • the avermectin compounds are so lubilized into the final composition thanks to their solubilization into the active phase.
  • ivermectin is so lubilized and stabilized in the fatty drops of the emulsion.
  • ivermectin is so lubilized and stable in the present composition which does not comprise or very few so lid fatty substances .
  • the composition according to the invention comprises less than 3 % by weight of solid fatty substances at room temperature and at atmospheric pressure, relative to the total weight of the composition.
  • Solid fatty substance means a compound which is so lid at room temperature and at atmospheric pressure and inso luble in water, that is to say a so lubility at room temperature and at atmospheric pressure of less than or equal to 1 % by weight relative to water.
  • the so lid fatty substances are chosen from fatty acids, fatty alcohols, waxes, gums, and mixtures thereof.
  • fatty acid mention may be made of lino leic acid, stearic acid.
  • fatty alcoho l As a fatty alcoho l, mention may be made of stearyl alcoho l, cetostearyl alcohol and cetyl alcohol.
  • wax mention may be made o f beeswax, carnauba wax, paraffin wax and candelilla wax.
  • the composition does not comprise stearyl alcoho l and cetyl alcohol.
  • the dermatological or pharmaceutical composition according to the invention comprises less than 3 % by weight, preferably, less than 2.5 % by weight o f so lid fatty substances at room temperature and at atmospheric pressure, relative to the total weight of the composition.
  • the dermatological or pharmaceutical composition does not comprise so lid fatty substances at room temperature and at atmospheric pressure.
  • the dermatological or pharmaceutical composition comprises less than 4% by weight, preferably less than 3 % by weight of liquid fatty substances at room temperature and at atmospheric pressure, relative to the total weight of the composition.
  • Liquid fatty substance means a compound which is liquid at room temperature and at atmospheric pressure and inso luble in water, that is to say a so lubility at room temperature and at atmospheric pressure of less than or equal to 1 % by weight relative to water.
  • avermectin compounds that are used according to the invention are preferably chosen from ivermectin, invermectin, avermectin, abamectin, doramectin, eprinomectin and selamectin.
  • the avermectin compound is ivermectin.
  • composition according to the invention comprises preferably from 0.01 to 10% by weight, more preferably from 0. 1 to 5 % by weight of avermectin compounds, relative to the total weight of the composition.
  • the dermatological or pharmaceutical composition according to the invention comprises at least one solvent and/or propenetrating agents of avermectin compounds.
  • a so lvent of avermectin compounds is defined as a liquid compound in which the compounds o f the avermectin family, in particular ivermectin, have a so lubility at room temperature and at atmospheric pressure of more than or equal to 2% by weight relative to the composition comprising only said so lvent or said so lvent in association with one or more solvents of avermectin compounds .
  • Solubility o f a compound into one or more so lvents is defined as the amount of compound that passes into a solution constituted of the one or more so lvents to achieve a saturated solution at constant temperature and pressure (stirring o f the saturated solution from 16 to 24 hours). Solubility is expressed in terms o f maximum vo lume or mass of the compound that dissolves in a given vo lume or mass of one or more solvents .
  • a propenetrating agent o f avermectin compounds makes it possible to facilitate the penetration of the compounds o f the avermectin family into the skin, preferably dissolves said compounds present in the composition according to the invention.
  • so lvents and propenetrating agents o f avermectin compounds are chosen from propylene glyco l, ethanol, isopropano l, butano l, N-methyl-2-pyrrolidone, dimethylsulfoxyde, polysorbate 80, poloxamer 124, phenoxyethano l, o leyl alcoho l, isostearic acid, diisopropyl adipate, PPG- 15 stearyl ether, octyl dodecanol, ethyl oleate, C 1 2 -C 1 5 alkyl benzoate and mixtures thereof.
  • so lvents and propenetrating agents are chosen from a mixture of propylene glycol and o leyl alcoho l.
  • the dermatological or pharmaceutical composition according to the invention preferably comprises from 1 to 10% by weight, preferably from 3 to 7% by weight o f so lvents and propenetrating agents of avermectin compounds, relative to the total weight of the composition.
  • composition according to the invention may comprise one or more surfactants.
  • the surfactants are chosen from non-ionic surfactants.
  • the surfactants are chosen from polyoxyethylenated fatty alcohol ethers, sorbitan esters, and mixtures thereof.
  • ceteareth-20 As a polyoxyethylenated fatty alcohol ether, mention may be made of ceteareth-20.
  • sorbitan esters mention may be made of sorbitan monostearate.
  • the dermatological or pharmaceutical composition according to the invention may comprise from 0.1 to 10% by weight, preferably from 1 to 7% by weight of surfactants, relative to the total weight of the composition.
  • composition according to the invention may also comprise at least one gelling agent, preferably at least one aqueous phase gelling agent.
  • carboxyvinyl polymers (carbomers) and, by way of non-limiting examples, of carbomer, Carbopol 981, Carbopol ETD 2020, Carbopol 980, Carbopol Ultrez 10 NF and Pemulen TR1, marketed by Lubrizol.
  • the gelling agents are chosen from acrylates/Cio-30 alkyl acrylate crosspolymer (Pemulen TR1).
  • gelling agent use will preferably be made of carbomers, and preferably Pemulen TR1.
  • composition of the invention preferentially contains from
  • the gelling agents are in the aqueous phase of the composition.
  • the aqueous phase of the composition according to the invention comprises water.
  • composition according to the invention may also contain inert additives or combinations o f these additives, such as flavor enhancers; preservatives; stabilizers; humidity regulators; pH regulators; osmotic pressure modifiers; UV-A and UV-B screening agents; and antioxidants.
  • inert additives or combinations o f these additives such as flavor enhancers; preservatives; stabilizers; humidity regulators; pH regulators; osmotic pressure modifiers; UV-A and UV-B screening agents; and antioxidants.
  • additives may be present in the composition at from 0.001 to 20% by weight relative to the total weight of the composition.
  • composition according to the invention comprises at least one active phase and at least one aqueous phase.
  • the composition according to the invention is suited for treating the skin and can be in liquid, pasty or so lid form, and more particularly in the form o f ointments, creams, milks, pomades, powders, impregnated pads, syndets, towelettes, so lutions, gels, sprays, foams, suspensions, lotions, sticks, shampoos or washing bases.
  • It may also be in the form o f suspensions o f microspheres or nanospheres or of lipid or polymeric vesicles or of po lymeric patches and of hydrogels for controlled release.
  • composition according to the invention comprises preferably from 5 to 95 % of active phase and from 5 to 95 % o f aqueous phase, more preferably said composition comprises from 5 to 30%) of active phase and from 70 to 95 % of aqueous phase.
  • the pH will preferably range from 5.0 to 7.0, more preferably from 6.0 to 6.5.
  • Verification o f the natural pH o f the mixture and possible correction with a so lution o f a neutralizing agent, and also the incorporation o f the optional additives, may be carried out, according to their chemical nature, during one o f the steps o f the method o f preparation, described below.
  • the composition according to the invention has a viscosity ranging from 1000 to 10000 cP, preferably from 1500 to 5000 cP measured at room temperature using a Brookfield LV.
  • the composition according to the invention has a yield stress ranging from 5 Pa to 50 Pa, preferably from 10 to 20 Pa at room temperature using a Malvern rheometer.
  • composition according to the invention comprises :
  • At least one active phase comprising from 0.01 to 10% by weight, preferably from 0. 1 to 5 % by weight, relative to the total weight of the composition, of avermectin compounds and from 1 to 10% by weight, preferably from 3 to 7% by weight o f so lvents and propenetrating agents of avermectin compounds,
  • composition comprises less than 3 % by weight o f so lid fatty substances .
  • composition according to the invention comprises :
  • At least one active phase comprising from 0.01 to 10% by weight, preferably from 0. 1 to 5 % by weight, relative to the total weight of the composition, of avermectin compounds and from 1 to 10%) by weight, preferably from 3 to 7% by weight o f so lvents and propenetrating agents of avermectin compounds,
  • composition comprises less than 3 % by weight o f so lid fatty substance chosen from fatty acids, fatty alcoho ls, waxes, gums, and mixtures thereof.
  • avermectin compound is preferably ivermectin.
  • the composition preferably comprises at least one gelling agent chosen from acrylates/C i o - 30 alkyl acrylate crosspolymer.
  • the composition preferably comprises one or more surfactants .
  • composition comprises :
  • At least one active phase comprising at least one active compound chosen from avermectin compounds
  • composition does not comprises stearyl alcoho l and cetyl alco ho l.
  • the dermatolo gical or pharmaceutical composition according to the invention is preferab ly a topical compo sition.
  • composition according to the invention is useful to treat dermatological conditions/afflictions .
  • composition according to the invention is useful for the treatment o f rosacea, o f common acne, o f seborrheic dermatitis, o f perioral dermatitis, o f acneiform rashes, o f transient acantho lytic dermatosis, o f acne necrotica miliaris and o f atopic dermatitis .
  • the dermatolo gical or pharmaceutical composition is used in the treatment of ro sacea.
  • the composition according to the invention is useful in a method for the treatment of ro sacea characterized in that the composition is administered topically.
  • the present invention also features a method for preparing the composition which comprises the following step :
  • the comparative composition 1 is formulated according to the fo llowing procedure : In a first beaker, weigh the carbomer (Pemulen TR1 ) polymer and the purified water, mix at 700 rpm and heat to 65°C ( ⁇ 2°C) then weigh the rest of the ingredients of the aqueous phase and mix all the aqueous phase. In a second beaker, weigh the fatty phase without sorbitan monostearate, dimethicone, propyl parahydroxybenzoate, and heat at 65 °C ( ⁇ 2°C) then weigh sorbitan monostearate and mix together. Weigh dimethicone and propyl parahydroxybenzoate then mix all the fatty phase.
  • composition 2 according to the invention is formulated according to the following procedure : In a first beaker, weigh the carbomer polymer (Pemulen TR 1 ) and the purified water, mix at 700 rpm and heat to 65°C ( ⁇ 2°C) then weigh the rest of the ingredients of the aqueous phase and mix all the aqueous phase.
  • the Yield stress is measured by the use o f a Rheometer CVO I OO Malvern (Cone Plan CP4°40mm) with a controlled stress sweep from 0.03 up to 300 Pa.
  • the viscosity o f the composition 2 according to the invention is quite low. Moreover, the yield stress of the composition 2 is lower than the one o f the composition 1 . Consequently, the composition 2 according to the invention is pourable. Physical stability
  • the table below represents physical stability o f composition 2 according to the invention at 5 °C, room temper (RT) and 40°C during three months.
  • composition 2 according to the invention is physically stable three months at 5 °C , room temperature (RT) and 40°C .
  • the table below represents chemical stability o f composition 2 according to the invention at room temperature and 40°C during 3 months.
  • Composition 2 is chemically stable three months at room temperature and 40° C .

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dispersion Chemistry (AREA)
  • Dermatology (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne une composition dermatologique ou pharmaceutique comprenant au moins une phase aqueuse et au moins une phase active comprenant au moins un composé actif choisi parmi des composés d'avermectine et au moins un solvant et/ou un agent propénétrant de composés d'avermectine, la composition comprenant moins de 3 % en poids d'un corps gras solide à température ambiante et à pression atmosphérique, par rapport au poids total de la composition. L'invention concerne également la composition destinée à être utilisée dans le traitement de la rosacée, de l'acné vulgaire, de la dermatite séborrhéique, de la dermatite périorale, d'éruptions cutanées acnéiformes, de la dermatose acantholytique transitoire, de l'acné nécrotique miliaire et de la dermatite atopique, et de préférence destinée à être utilisée dans le traitement de la rosacée. L'invention concerne enfin un procédé de préparation de la composition.
PCT/EP2017/080146 2016-11-24 2017-11-23 Composition comprenant des composés d'avermectine sans corps gras solides WO2018096008A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US16/463,810 US10744147B2 (en) 2016-11-24 2017-11-23 Composition comprising avermectin compounds without solid fatty substances
EP17803935.0A EP3544587A1 (fr) 2016-11-24 2017-11-23 Composition comprenant des composés d'avermectine sans corps gras solides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP16306555.0A EP3326608A1 (fr) 2016-11-24 2016-11-24 Composition comprenant des composés d'avermectine sans matières grasses solides
EP16306555.0 2016-11-24

Publications (1)

Publication Number Publication Date
WO2018096008A1 true WO2018096008A1 (fr) 2018-05-31

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Application Number Title Priority Date Filing Date
PCT/EP2017/080146 WO2018096008A1 (fr) 2016-11-24 2017-11-23 Composition comprenant des composés d'avermectine sans corps gras solides

Country Status (3)

Country Link
US (1) US10744147B2 (fr)
EP (2) EP3326608A1 (fr)
WO (1) WO2018096008A1 (fr)

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CA3199736A1 (fr) 2020-11-23 2022-05-27 Sight Sciences, Inc. Formulations et procedes de traitement d'affections de l'?il
EP4062907A1 (fr) 2021-03-23 2022-09-28 Substipharm Formulation par voie orale d'ivermectine et utilisations

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US5773422A (en) * 1996-01-29 1998-06-30 Komer; Gene Avermectin formulation
US20050143325A1 (en) * 2002-02-08 2005-06-30 Guzzo Cynthia A. Topical invermectin composition
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US20090233877A1 (en) * 2006-09-28 2009-09-17 Galderma S.A. Avermectin compounds and treatment of dermatological disorders therewith
US20090264378A1 (en) * 2006-09-28 2009-10-22 Galderma S.A. Avermectin compounds and treatment of dermatological disorders in humans therewith
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US10744147B2 (en) 2020-08-18

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